N,N'-Dimethylethylenediamine → HCID 67036298, compound

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 3-(1-phenyl-ethylidene)-1,3-dihydro-indol-2-one (352.7 mg, 1.5 mmol), and K2CO3 (276 mg, 2.0 mmol), evacuated, and backfilled with argon. N,N′-dimethylethylenediamine (11 uL, 0.10 mmol, 10 mol %), ethyl 3-iodobenzoate (278.8 mg, 1.01 mmol), and acetonitrile (1.5 ml) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 80° C. for 23 h. The reaction was monitored by HPLC. When the reaction was finished, the solvent was removed under reduced pressure. The residue was separated by flash chromatography column (gradient elution, 5-10% ethyl acetate in petroleum ether) to give 3-[2-oxo-3-(1-phenyl-ethylidene)-2,3-dihydro-indol-1-yl]-benzoic acid ethyl ester as yellow powder (344 mg, 90%). 1H NMR (400 MHz, CDCl3) δppm 1.42 (t, J=7.20 Hz, 3H) 2.87 (s, 3H) 4.42 (q, J=7.07 Hz, 2H) 6.25 (d, J=7.58 Hz, 1H) 6.68-6.78 (m, 2H) 7.09 (t, J=7.71 Hz, 1H) 7.34-7.40 (m, 2H) 7.47-7.58 (m, 3H) 7.62-7.72 (m, 2H) 8.11-8.19 (m, 2H). MS calcd. for C25H21NO3 383, obsd. (ESI+) [(M+H)+] 383.9.

Provenance & Evidence